


tigerlily

by sayjerk



Category: Supernatural
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2013-05-28
Updated: 2013-05-28
Packaged: 2017-12-13 07:15:19
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 2,191
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/821510
Author URL: https://archiveofourown.org/users/sayjerk/pseuds/sayjerk
Summary: <blockquote class="userstuff">
              <p>Dean's got a girl and Sam could care less. Really. (Sam: 14, Dean: 18)</p>
            </blockquote>





	tigerlily

——

Sam tries really, really hard not to hate Penelope Brossard just because she’s hooking up with Dean but she runs her fingers over Dean’s jacket and tugs at the collar, smoothing out wrinkles like she’s his goddamn wife, and Sam’s sense of goodwill only extends so far. 

He doesn’t have to see her much, but Dad’s on a hunt and Dean’s got himself a job at the convenience store that unfortunately has a really good collection of comic books.

And, therefore-

“Babe, let’s recheck the inventory,” Penelope says, pressing her breasts up against Dean and licking her lips. Sam makes a distasteful noise that doesn’t go unnoticed by Dean, who simply raises an eyebrow at Sam before tugging Penelope to the back of the store. 

Fine, whatever. Penelope and Dean can go fuck themselves- or, well, each other. Not like Sam cares. Not like Dean spent last night tracing Sam’s spine with his tongue.

He throws the comic he had been pretending to read on the counter and makes a whole lot of noise on his way out, yells, “No one’s watching the fucking cash register, jackass.”

It all goes pretty much unnoticed and Dean  _better_  suck him off tonight.

-

“Penelope’s stupid.”

He mumbles it around a spoonful of cereal so he’s almost hoping Dean won’t hear, except he does and it sucks because Dean has that dumb, cocky look on his face. So maybe Sam’s jealous, but it’s not like Dean’s got room to judge considering he almost killed Matt Dayringer when he overheard the senior trying to ask Sam out. 

“Yeah, but she’s hot. Also, dude, cheerleader. Flexible. _Short skirt_.”

“You’re a pig,” Sam says, scrunching up his nose and trying to find a way to stab his spoon into milk that doesn’t look childish and petulant. 

“And, you’re jealous.”

Sam snorts, feeling his face heat up, and gets up from the table to toss his bowl angrily into the sink. 

“Of Casey? Un-fucking-likely, jerk.”

Dean hooks an arm around Sam’s neck from behind and rubs his knuckles into the top of Sam’s head. He presses his mouth against Sam’s ear and whispers,  _Bitch_ , like it’s a term of endearment. Sam’s skinny and at least six inches shorter than Dean, but he wiggles out of the hold easily and aims a kick right against Dean’s shin. 

He tries not to grin too much when Dean shouts off a curse and limps across the kitchen until he can sit down in a chair.

-

Sam has made exactly one friend since they moved to South Fork, Indiana, and it’s Ashley Lockheart. She’s got pitch black hair, the prettiest smile in the world (after Dean’s, obviously), leather boots she wears all the time, and a kickass attitude that makes Sam like her instantly. There’s also the fact that she seems to pretty much be an outcast and Sam’s always taken a liking to outcasts. 

Kindred spirits and all that.

Either way, she’s his only friend and he wishes he’d made at least one more because when he awkwardly shares his Dean issues with her ( _this guy I’m seeing, you don’t know him_ ), her advice is sort of out of Sam’s comfort zone.

“Well, you  _just_  said he likes cheerleaders,” Ashley says, chewing absently on a pen as her homework slips off her lap. Sam glares at her, but she’s preoccupied with picking up her papers off the grass and flipping off the group of girls that cough the word ‘slut’ as they walk past her. 

Lunch break doesn’t end for another fifteen minutes so he’s stuck trying to reason against Ashley fucking Lockheart.

“I’m not dressing up as a cheerleader,” he grits out, spitting each word out like it did him personal harm. “That’s stupid and also embarrassing.”

Ashley shrugs, messy black hair falling into her eyes, and Sam really ought to have made more friends.

-

Penelope is suddenly over a lot more and Sam suspects Dean is just trying to get a rise out of him, so he counters every Penelope interaction with spending time at Ashley’s house.

Which turns out to be to his disadvantage because Ashley dug up her sister’s cheer uniform and has it laid out on her bed. 

“No.”

Ashley pouts.

” _No_.”

Ashley hangs her head and fingers at the edge of her shirt.

“Fine.  _Fuck_.”

Ashley giggles and it’s the single more horrifying sound Sam has ever heard. Well, that and the zipper on a skirt going up.

-

Ashley keeps insisting Dean is gonna love it ( _I know how boys work, Sam, trust me_ ) but Sam feels foolish and awkward as he sits on Dean’s bed in a fucking skirt with a big, red dildo up his ass. He keeps fidgeting and swallowing as a lump forms at his throat. Dad’s gone for at least three more days and Dean’s shift at the store ends in ten minutes. 

He takes in deep breathes and tries to remember all the tips Ashley gave him.

He’s practicing how to arch his back in a way that’s supposedly great for showing off your ass when the door slams open and shut. He scrambles off the bed and paces around the room in mild panic.

After a few seconds, he hears Dean yell his name. 

He hears his own room’s door open and then Dean yells his name again, this time with confusion and slight trace of anger.

“Where the fuck-“

Dean stops mid motion, one step inside the room and his hand clenched around the door handle. Sam stops his pacing immediately and wrings his hands together as Dean’s mouth opens mutely. He’s developing some intense insecurities as Dean struggles to form words.

Ashley’s sister was sixteen when she wore the uniform so the red, white, and black shirt is a bit small, exposing an inch of his belly, but the skirt fits him almost obscenely well. Which is sort of the main point, he supposes.

“Holy fuck,” Dean breathes out, hand slipping off the door handle as he stumbles forward a step. Sam swallows nervously, breaking out in goosebumps, and he’s about to come up with some stupid story about how Ashley  _made him_  and he didn’t _want_  to when Dean steps forward and-

“Holy fuck,” he whispers against Sam’s mouth, cupping his face with both hands, “Jesus, Sammy.”

Dean slips a hand around his neck and down his back and settles it right over Sam’s ass, smooths his palm across it reverently, misplacing the pleats Ashley had meticulously ironed this afternoon. Dean tips Sam’s head up by nudging a knuckle under Sam’s chin. He looks dazed and turned on and like if Sam asked about Penelope, Dean wouldn’t even remember her. It makes Sam smile with satisfaction and petty triumph. 

“How the fuck,” he says, a little out of breath, and Sam simply says, “Ashley.”

“Gonna have to buy that girl flowers,” Dean says, grinning disarmingly, and Sam laughs.

-

After a few minutes of simply worshipping the attire, Dean asks Sam to kneel on the bed. 

“On your hands and knees, if you don’t mind,” he instructs and really, this was supposed to be Sam’s way of getting back at Dean, not Dean’s personal Christmas. 

“That’s cute that you think I’m just-“

The rest of his well-worded and justified comment gets eaten up by Dean’s mouth which is hot and insistent against his own. Dean pushes at his stomach, pulling his legs out from under him as Sam falls backwards on the bed with his breath knocked out of him. He blinks stupidly up at Dean when he crawls on top of him and balances himself on his elbows.

“You dressed up real pretty for me, Sam,” he says in that deep, dumb voice that always makes Sam shiver. 

“Well, you’ve been so  _busy_  lately with  _Penelope_. Just wanted you to notice.”

It sounds a bit too much like a confession, too much like a clingy boyfriend that needs reassurance constantly, and Sam instantly regrets it. That is, until Dean’s face softens and he bends down to press a soft kiss on his forehead.

“Could never not notice you, Sammy. Think about you all the time.”

Sam’s heart jerks painfully and he closes his eyes as Dean trails kisses down his face and neck and collarbone and oh fuck.

Dean grips his waist, drags his hand down Sam’s thigh and then drags it up until the skirt is pushed away and the skimpy, lace panties Ashley made him put on are on display.

“Christ,” Dean grounds out almost absently, wriggling down the bed until he’s face level with Sam’s dick. He presses a kiss against Sam’s thigh, right under where the panties end, and Sam squirms helplessly. 

He ghosts teasing fingers across Sam’s hard-on, chuckling cheerfully when Sam makes a distressed noise. Says, “Patience,” and sits up on his knees. He then flips Sam over onto his stomach in one swift (hot as hell, really, but fuck if Sam’s gonna admit it) movement. Sam presses his face into Dean’s pillow and Dean latches onto his hips, pulls until Sam gets the idea and positions himself on his forearms and knees. 

“Beautiful,” Dean praises, palming his ass and flipping the pleats out of the way to get at his underwear. He drags the lace down Sam’s legs and leaves it at his knees. 

Sam shudders, making noises he’s embarrassed about and feeling better about it when Dean makes them too. 

“Oh, fuck.”

“Guess you found the dildo,” Sam says and it doesn’t come off as sultry as he’d been instructed, but Dean seems too preoccupied to notice.

“Oh,  _fuck_.  _Sammy_.”

He feels Dean push the dildo in deeper and he keens, palms sweating as they clench the bedsheet under him. Dean pumps the dildo a little, gently, and Sam bites into his lip to keep from yelling. 

” _God_.”

“Please, just. Dean, I-“

“Yeah, yeah. Fuck.”

The dildo is pulled out of him slowly and Dean blankets himself over Sam, kissing the top of his spine to distract him from the emptiness. Sam unclenches a fist to bring it around Dean’s neck and he moans loud and needy as Dean replaces the dildo with two finger. 

His skin feels too tight, like it’s going to break his bones, and he wants Dean to make it feel like that all the time, keep crooking his fingers and working them in and out. 

“Please,” Sam says, all but begging, and Dean answers with another finger. Sam doesn’t need stretching, he did that himself in the bathroom half an hour ago with shaky fingers and Dean’s name on his lips, so he tells Dean to hurry up, please, please,  _please_.

Dean lifts off of Sam’s back and steadies a hand on Sam’s hip as he presses inside. 

They both make a noise at the sensation and Dean fists a hand into the fabric of the skirt, uses the hold to move Sam’s hips back. 

“Jesus fucking  _Christ_ ,” he whispers, pushing in further.

They’ve had sex enough times, but this feels different. This feels another kind of wrong, another kind of dirty, another kind of thrilling. Sam can barely breathe under the heat.

“Fuck me,” he says high and whiny like in the porn Dean watches. It’s utterly barbaric and Sam is going to synthesize this situation later, but at the moment all he cares about is getting fucked.

Dean starts working in and out, slow and smooth, and then a little bit faster when Sam bitches about it. 

_Should have fucked your mouth first._

_As if I- oh, fuck, yes, right there._

Sam feels Dean grip loosen from the skirt, feels him tug the skirt right and smooth the pleats down. He then teases the edge of Sam’s shirt, dipping calloused fingers into his skin and pressing so hard that there will be little marks there tomorrow. Something for Dean to mouth at when they’re fucking on the kitchen counter.

Dean grabs his hips with both hands and slams in hard, fast, and hot as all hell. Doesn’t let up. And, Sam finds himself coming.

“Fuck, there we go. That’s a good boy. Didn’t even have to touch, huh, Sammy?”

Sam barely even hears him, too busy coming all over the sheets and panting helplessly agains the pillow. Dean thrusts in and out even harder, yanking at Sam’s hair and tweaking his nipples from behind. Sam twists his hips upward and Dean slaps a hand down on his ass, grunts loudly as his pace quickens. 

He makes a desperate little noise that Sam will most likely jerk off to some other day and comes inside Sam with a few, long thrusts. 

They fall to their sides and Dean curls a hand around Sam’s waist, pinky tucked into the skirt. 

“Fuck.”

-

“Shut the fuck up.”

Ashley grins. “I didn’t even say anything.”

Sam throws a pencil at her and she dodges, giggling as she tosses her hair over her shoulder. She gets a weird look on her face and Sam begins to feel a bit anxious.

“Now, how would Dean feel about a naughty nurse outfit?”

Sam  _really_  should have made more friends.

-


End file.
